Cyclohexadienone derivatives possessing α-D-glucopyranosyl moiety were designed and synthesized using chemical oxidation or electrochemical oxidation with boron-doped diamond electrode in the final stage. In the chiral induction studies, catalytic hydrogenation provided high diastereoselectivity (dr ratio: > 9:1). Conformational analyses of the C-glucoside structures were performed by NOE experiments and force field calculations, and supported the observed regio-selectivity.
- Anodic oxidation
- Boron-doped diamond electrodes
- Diastereoselective hydrogenation
- Hypervalent iodobenzene
ASJC Scopus subject areas
- Drug Discovery
- Organic Chemistry